Methyl iodide → HCID 58827278, compound

Participants

Reaction Steps

To a stirred solution of [2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylamino]acetic acid (0.66 g, 2.0 mmol) in DMF (20 mL), were added methyl iodide (0.34 g, 2.4 mmol) and potassium carbonate (0.33 g, 2.4 mmol). The mixture was stirred overnight at room temperature. The solvent was evaporated in vacuo, giving a yellow oil. The oil was dissolved in CH2Cl2 (100 mL), washed with sat. aq. sodium bicarbonate (100 mL), water (100 mL) and brine (100 mL), and dried (MgSO4). The solvent was evaporated in vacuo to give a yellow solid. This material was triturated with diethyl ether and then filtered, and the resulting solid was chromatographed, eluting with 9:1 methylene chloride-ethyl acetate. The resulting solid was triturated in 1:1 ethyl ether-water, filtered, and dried under high vacuum, providing 0.42 g (61%) of the product as a yellow solid: mp 210-212° C.; 1H NMR (DMSO-d6) δ 2.03-2.07 (m, 1H), 2.47-2.63 (m, 2H), 2.96-2.83 (m, 1H), 3.69 (s, 3H), 4.23 (d, J=6.0 Hz, 2H), 5.08 (dd, J=12.4 Hz, J=5.2 Hz, 1H), 6.91-7.11 (m, 3H), 7.61 (t, J=7.7 Hz, 1H), 11.12 (s, 1H); 13C NMR (DMSO-d6) δ 22.10, 30.96, 43.62, 48.51, 51.90, 109.76, 111.22, 117.65, 132.01, 136.09, 145.76, 167.21, 168.70, 170.12, 170.65, 172.77; Anal. calcd. for C16H15N3O6: C, 55.65; H, 4.38; N, 12.17. Found: C, 55.64; H, 4.28; N, 11.98.

Provenance & Evidence